This invention relates to alkyl sulfones which are useful as agricultural chemicals.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR2## wherein R is butyl, phenyl or ##STR3## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent.
Wojciechowski, J. Acta, Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR4## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR5## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA0 R'=Et, Pr, Me.sub.2 CH, Bu ##STR10## in 2-, 3- and 4-position. PA0 R'=alkylcarbamoyl, cyclohexylcarbamoyl, arylcarbamoyl, CSNHCH.sub.2 CH.dbd.CH.sub.2, CONHC.sub.6 H.sub.4 Cl-p, alkylthiocarbamoyl, H, COEt; PA0 R.sup.2 =H, Me; PA0 X=NH, NMe, O, S, NEt; and PA0 n=0, 1. PA0 R.sup.1 =SH, SR, SO.sub.2 R or Cl; and PA0 R.sup.2 =Cl, SH or SO.sub.2 C.sub.2 H.sub.5. PA0 R is CHF.sub.2, CF.sub.3, CH.sub.2 CF.sub.3, CF.sub.2 CHFG, G being F, Cl, Br or CF.sub.3. PA0 n is 0, 1 or 2. PA0 A is OR.sub.3, CH.sub.2 OR.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3, S(O).sub.p R.sub.3, CH.sub.2 S(O).sub.p R.sub.3, CO.sub.2 R.sub.3, CH.sub.2 CO.sub.2 R.sub.3, CN, CH.sub.2 CN, ##STR18## CH.sub.2 OH, CH(OH)CH.sub.3, CH.sub.2 CH.sub.2 OH, C(O)CH.sub.3, CH.sub.2 C(O)CH.sub.3, CHO, CH(OCH.sub.3).sub.2 or ##STR19## R.sub.1 and R.sub.4 are independently H, F, Cl, Br, CH.sub.3, OCH.sub.3, CF.sub.3 or NO.sub.2 ; PA0 R.sub.2 is H or CH.sub.3 ; PA0 R.sub.3 is C.sub.1 -C.sub.2 alkyl; PA0 n is 0, 1 or 2; PA0 p is 0, 1 or 2; PA0 X is CH.sub.3, OCH.sub.3 or Cl; PA0 Y is CH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; and PA0 Z is CH or N; PA0 (1) when X is Cl then Z is CH; PA0 (2) when X is Cl and Y is CH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 then A is OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3, CO.sub.2 R.sub.3, CH.sub.2 CO.sub.2 R.sub.3, CN, CH.sub.2 CN, ##STR20## CH.sub.2 OH, CH(OH)CH.sub.3, CH.sub.2 CH.sub.2 OH, C(O)CH.sub.3, CH.sub.2 C(O)CH.sub.3, CHO, CH(OCH.sub.3).sub.2 or ##STR21## (3) when X is Cl and A is OR.sub.3, CH.sub.2 OR.sub.3, S(O).sub.p R.sub.3 or CH.sub.2 S(O).sub.p R.sub.3, then Y is NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2. PA0 (1) Compounds of Formula I where A is OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3, CO.sub.2 R.sub.3, CH.sub.2 CO.sub.2 R.sub.3, CN, CH.sub.2 CH.sub.2 CN, CH(OH)CH.sub.3, ##STR22## CH.sub.2 OH, CH.sub.2 CH.sub.2 OH, C(O)CH.sub.3, CH.sub.2 C(O)CH.sub.3, CHO, CH(OCH.sub.3).sub.2 or ##STR23## (2) Compounds of Preferred 1 where A is CO.sub.2 R.sub.3 or CN; R.sub.1 is H; and X is not Cl. PA0 (3) Compounds of Formula I where Y is NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2. PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfonyl)ben zenesulfonamide; PA0 2-(2-methoxyethylsulfonyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbon yl]benzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfonyl)be nzenesulfonamide; PA0 N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfony l)benzenesulfonamide; PA0 2-(2-methoxyethylsulfonyl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminoc arbonyl]benzenesulfonamide; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxyethylsulfon yl)benzenesulfonamide; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benzenesul fonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benz enesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benzenesu lfonamide; PA0 N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benze nesulfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyanomethylthio )benzenesulfonamide; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(cyanomethylthio)benz enesulfonamide; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(2-(methoxy-2-oxoethylsulfo nyl)benzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(2-methoxy-2-oxoethylsulfo nyl)benzenesulfonamide; and PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-methoxy-2-oxo ethylsulfonyl)benzenesulfonamide.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. drug Res. 6, 123 (1974), ##STR6## wherein R is pyridyl.
In U.S. Ser. No. 029,821 now abandoned, herbicidal compounds such as N-heterocyclic-N'(arylsulfonyl)carbamimidothioates (or compounds wherein a thienyl radical is substituted for the aryl radical), such as methyl N'-(2-chlorophenyl)sulfonyl)-N-(4-methoxy-6-methylpyrimidin-2-yl)carbamimi dothioate are taught.
U.S. Pat. No. 3,689,549 to R. P. Williams discloses "heterocyclic sulfonamides wherein the heteroatoms are inert can be used, e.g., compounds having the furan, thiophene or pyridine nucleus," in the production of sulfonyl isocyanates from sulfonamides in a sulfolane solvent.
B. G. Boggiano, V. Petrow, O. Stephenson and A. M. Wild, in Journal of Pharmacy and Pharmacology 13, 567-574 (1961) disclose the following compounds which were tested for hypoglycemic activity. ##STR7## where ##STR8## is in the 2 or 3 position.
J. Delarge in Acta Pol. Pharm. 34, 245-249 (1977) discloses N-alkylcarbamoylpyridinesulfonamides, as described in the structure below, as mild antiinflammatory agents and strong diuretics. ##STR9## R=3-, 4-, 5-, 6-Me, 2-, 4-, 6-Cl, 3-Br, 4-Et.sub.2 N, 4-Me.sub.2 CHNH, 4-(3-ClC.sub.6 H.sub.4)NH, 4-(3-CF.sub.3 C.sub.6 H.sub.4)NH;
German Pat. No. 2,516,025 (Nov. 6, 1975) to J. E. Delarge, C. L. Lapiere and A. H. Georges discloses the following compounds as inflammation inhibitors and diuretics. ##STR11## R=C.sub.6 H.sub.4 R.sup.3 (R.sup.3 =Cl, CF.sub.3, Me, MeO, H, Br, F, NO.sub.2, Et, NH.sub.2), Et, iso-Pr, 4-methylfuryl, C.sub.6 H.sub.3 Cl.sub.2 --, C.sub.6 H.sub.3 (CF.sub.3)Cl;
U.S. Pat. No. 3,346,590 (Oct. 10, 1967) (to K. Dickere and E. Kuhle) disclose the following pyridinesulfonyl isothiocyanates as novel compounds. ##STR12##
Chem. Abstr. 83 163951p (1975) reports preparation of several 3-substituted 2-alkylsulfonylpyridines: ##STR13## wherein R=CH.sub.3 or C.sub.2 H.sub.5 ;
Compound II with R.sup.1 =SO.sub.2 C.sub.2 H.sub.5 is reported to give 96.9% inhibition of gluconeogenesis in rat renal cortex tissue.
U.S. Pat. No. 4,127,405 and U.S. Pat. No. 4,169,719 discloses herbicidal sulfonylureas of the general structure: ##STR14## where, among others R.sub.3 is CH.sub.3 S(O).sub.n or C.sub.2 H.sub.5 S(O).sub.n, n being 0, 1 or 2.
U.S. Ser. No. 152,021 pending discloses herbicidal sulfonylureas of the general formula: ##STR15## where A is S(O).sub.n, n being 0, 1 or 2; and
U.S. Ser. No. 227,886 discloses herbicidal sulfonylureas of the general formula: ##STR16## where R.sub.3 is C.sub.3 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopropylmethyl or cyclopentyl; and
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.